Obama first breached the subject when he spoke of a recent interview he had with a columnist about his refusal to use the phrase "radical Islam."

He said:

"And this is a columnist who is generally sympathetic and a thoughtful person but actually thought that I was underestimating the importance of having this pithy phrase that includes 'Islam' to accurately label the nature of the threat. And he said, 'Well, you acknowledge all these truths, but you do it in long paragraphs, and that's not sufficient.' And I took the criticism to heart. But I responded to him, saying, 'I refuse to give in to the notion that the American people can't handle complicated information.'"

"Because I know the American people. I've met a lot of them. I've met a lot more of them than any columnist has, or any talking head on TV has. And they're pretty sophisticated. They're not always paying attention, and there's a lot of noise out there, but when they have the time, they're not looking to be spoken down to and there's no requirement to dumb things down. They get it."

"You think about the race speech that I gave in Philadelphia [in 2008] when the Jeremiah Wright stuff broke [regarding the Obamas' Chicago pastor]. That was a pretty complicated piece of business, but I think people heard me. Now there are filters, there are a lot of filters there, and so sometimes it's hard to get at folks. What I miss is just the fact that there's not a single conversation, but there is just this …"

Goodwin cut in to add that it would have been "easier" for Obama to get his message across if he only had to worry about the three television networks that had a monopoly on the earlier days of television — CBS, ABC, and NBC.

"Right," Obama said, later adding if he "just had [the benefits of] what [former President Ronald] Reagan had, then the concentrated power of the bully pulpit would be an enormous advantage."

"I think part of the reason that I have been successful, though, despite maybe not always fitting my message into the pre-packaged formulas, is there is this whole other media ecology out there of the Internet and Instagram and memes and talk shows and comedy, and I'm pretty good at that," he continued. "I [give] maybe the long-winded speeches that not everybody reads, but I can also do a slow jam on Jimmy Fallon better than most."

He said such appearances serve "a purpose" because he thinks he has good takes on pop culture, which he believes "makes up for the fact that I'm not a sound-bite politician for the nightly news."

"And as a consequence I think I'm able to reach a lot of folks, despite the fact that the conventional news media sometimes says, 'You know, this speech is too long,' or 'It's too complicated,' or 'He needs to have better sound bites,' or what have you," he said. "Because they're not seeing me on Between Two Ferns trying to sell the Affordable Care Act to young people, and the fact that we're getting millions of hits on something that is not on conventional TV."